Eicosapentaenoyl ethanolamide

CAT: 0804-HY-124089-01Size: 5 mg (144.71 mM x 100 μL in Ethanol)Dry Ice: NoHazardous: No

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CAT#:0804-HY-124089-01Size:5 mg (144.71 mM x 100 μL in Ethanol)

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Description

Eicosapentaenoyl ethanolamide, an omega-3 fatty acid, is one of N-acylethanolamines (NAEs) . Eicosapentaenoyl ethanolamide is cannabinoid CB1/CB2 receptor agonist. Eicosapentaenoyl ethanolamide acts as a metabolic signal. Eicosapentaenoyl ethanolamide inhibits dietary restriction (DR) -induced lifespan extension in wild type animals and suppresses lifespan extension in a TOR pathway mutant[1][2].

CAS Number

109001-03-8

UNSPSC

12352211

Hazard Statement

H225, H319

Target

Cannabinoid Receptor

Type

Reference compound

Related Pathways

GPCR/G Protein; Neuronal Signaling

Field of Research

Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/eicosapentaenoyl-ethanolamide.html

Concentration

144.71 mM * 200 μL in Ethanol

Purity

98.38

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

O=C(CCC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)NCCO

Molecular Formula

C22H35NO2

Molecular Weight

345.52

Precautions

H225, H319

References & Citations

[1]Mark Lucanic, et al. N-acylethanolamine signalling mediates the effect of diet on lifespan in Caenorhabditis elegans. Nature. 2011 May 12;473 (7346) :226-9.|[2]Iain Brown, et al. Cannabinoid receptor-dependent and -independent anti-proliferative effects of omega-3 ethanolamides in androgen receptor-positive and -negative prostate cancer cell lines. Carcinogenesis. 2010 Sep;31 (9) :1584-91.

Shipping Conditions

Blue Ice

Storage Conditions

Solution, -20°C, 2 years

Scientific Category

Reference compound1

Clinical Information

No Development Reported

Isoform

CB1; CB2

Chemical Information

(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine

(5Z,8Z,11Z,14Z,17Z)-icosapentaenoylethanolamine is an N-acylethanolamine 20:5 that is the ethanolamide of (5Z,8Z,11Z,14Z17Z)-eicosapentaenoic acid. It has a role as a PPARgamma agonist. It is a N-acylethanolamine 20:5 and an endocannabinoid. It is functionally related to an all-cis-5,8,11,14,17-icosapentaenoic acid.

CAS Number	109001-03-8
PubChem CID	5283450
IUPAC Name	(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide
Molecular Formula	C22H35NO2
Molecular Weight	345.5
XLogP	4.7
Topological Polar Surface Area	49.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Heavy Atom Count	25
Formal Charge	0
Complexity	445

SMILES

CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO

InChI

InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

InChIKey

OVKKNJPJQKTXIT-JLNKQSITSA-N

Chemical Structure

2D Structure

CAS: 109001-03-8

CID: 5283450

Formula: C22H35NO2

MW: 345.5

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	345.5
XLogP3	4.7
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	15
Exact Mass	345.266779359
Monoisotopic Mass	345.266779359
Topological Polar Surface Area	49.3 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	445
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	5
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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